Jess (Jess Harris) and Josh (Josh Schmidt) are best friends, housemates and twentysomething. While their friends finish uni degrees, climb the corporate ladder and settle down, Jess and Josh live for the weekend. When they find themselves unemployed, getting evicted and constantly dodging the dreaded question, "So what do you do with yourselves?", they decide it's time to become their own bosses. This 6-part comedy/drama series sees Jess and Josh set out each week in search of their big break.

An important ascpect of the overall feel of twentysomething is the music. The soundtrack largely consisting of local unsigned indie bands mainly sourced through triple j unearthed, supporting and reflecting the twentysomething lifestyle. Over the six episodes twentysomething features songs from local Melbourne bands, Big Scary, Jinga Safari, Love Connection, Red Ink, Loon Lake, Polygon Palace, 8 Bit Love and also tracks from Adelaide Bands, Hawks of Alba and the Keepsakes along with many more. The opening title track for the series Fear of Flying is by the much loved Australian Independent artist Dan Sultan. The music complements and enhances the world of Jess and Josh, giving the show its own unique and fresh sound.